Irinotecan HCl trihydrate
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MedKoo CAT#: 100480

CAS#: 136572-09-3 (HCl trihydrate)

Description: Irinotecan hydrochloride is the hydrochloride salt of a semisynthetic derivative of camptothecin, a cytotoxic, quinoline-based alkaloid extracted from the Asian tree Camptotheca acuminata. Irinotecan, a prodrug, is converted to a biologically active metabolite 7-ethyl-10-hydroxy-camptothecin (SN-38) by a carboxylesterase-converting enzyme. One thousand-fold more potent than its parent compound irinotecan, SN-38 inhibits topoisomerase I activity by stabilizing the cleavable complex between topoisomerase I and DNA, resulting in DNA breaks that inhibit DNA replication and trigger apoptotic cell death.


Price and Availability

Size
Price

100mg
USD 120
1g
USD 350
10g
USD 1650
100g
USD 6950
Size
Price

250mg
USD 250
2g
USD 450
20g
USD 2650
Size
Price

500mg
USD 350
5g
USD 750
50g
USD 4250

Irinotecan HCl trihydrate, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 30g may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100480
Name: Irinotecan HCl trihydrate
CAS#: 136572-09-3 (HCl trihydrate)
Chemical Formula: C33H45ClN4O9 E
Exact Mass:
Molecular Weight: 677.18
Elemental Analysis: C, 58.53; H, 6.70; Cl, 5.23; N, 8.27; O, 21.26


Related CAS #: 136572-09-3 (HCl trihydrate)   100286-90-6 (HCl)   97682-44-5 (Free base)    

Synonym: CPT11; CPT-11; CPT 11; U101440E; HSDB 7607; HSDB-7607; HSDB7607; camptothecin-11; irinotecan; irinotecan HCl; Bbrand name: Camptosa; Campto.

IUPAC/Chemical Name: (S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl [1,4'-bipiperidine]-1'-carboxylate hydrochloride trihydrate.

InChi Key: KLEAIHJJLUAXIQ-JDRGBKBRSA-N

InChi Code: InChI=1S/C33H38N4O6.ClH.3H2O/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2;;;;/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3;1H;3*1H2/t33-;;;;/m0..../s1

SMILES Code: O=C(N1CCC(N2CCCCC2)CC1)OC3=CC=C4N=C5C(CN6C(C(COC([C@@]7(CC)O)=O)=C7C=C65)=O)=C(CC)C4=C3.[H]Cl.[H]O[H].[H]O[H].[H]O[H]


Technical Data

Appearance:
Yellow solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Related CAS#
136572-09-3 (Irinotecan hydrocholide trihydrate);
100286-90-6 (Irinotecan hydrocholide);
97682-44-5 (Irinotecan Free base)


References

1: Schwartzman AD, Sethi R, Smith R. Multiorgan failure in a patient treated with the 5-fluorouracil, leucovorin, oxaliplatin, and irinotecan regimen. Clin Colorectal Cancer. 2013 Jun;12(2):136-9. doi: 10.1016/j.clcc.2012.09.005. Epub 2012 Oct 24. Review. PubMed PMID: 23098664.

2: Petitprez A, Larsen AK. Irinotecan resistance is accompanied by upregulation of EGFR and Src signaling in human cancer models. Curr Pharm Des. 2013;19(5):958-64. Review. PubMed PMID: 22973964.

3: Qi WX, Shen Z, Lin F, Sun YJ, Min DL, Tang LN, He AN, Yao Y. Overall survival benefits for irinotecan-containing regimens as first-line treatment for advanced gastric cancer: an updated meta-analysis of ten randomized controlled trials. Int J Cancer. 2013 Jan 15;132(2):E66-73. doi: 10.1002/ijc.27775. Epub 2012 Sep 1. Review. PubMed PMID: 22890856.

4: Carrillo JA, Munoz CA. Alternative chemotherapeutic agents: nitrosoureas, cisplatin, irinotecan. Neurosurg Clin N Am. 2012 Apr;23(2):297-306, ix. doi: 10.1016/j.nec.2012.01.005. Epub 2012 Feb 18. Review. PubMed PMID: 22440873.

5: Mollica A, Stefanucci A, Feliciani F, Cacciatore I, Cornacchia C, Pinnen F. Delivery methods of camptothecin and its hydrosoluble analogue irinotecan for treatment of colorectal cancer. Curr Drug Deliv. 2012 Mar;9(2):122-31. Review. PubMed PMID: 22283650.

6: Paulík A, Grim J, Filip S. Predictors of irinotecan toxicity and efficacy in treatment of metastatic colorectal cancer. Acta Medica (Hradec Kralove). 2012;55(4):153-9. Review. PubMed PMID: 23631285.

7: Di Paolo A, Bocci G, Polillo M, Del Re M, Di Desidero T, Lastella M, Danesi R. Pharmacokinetic and pharmacogenetic predictive markers of irinotecan activity and toxicity. Curr Drug Metab. 2011 Dec;12(10):932-43. Review. PubMed PMID: 21787264.

8: Jakobsen JN, Hasselbalch B, Stockhausen MT, Lassen U, Poulsen HS. Irinotecan and bevacizumab in recurrent glioblastoma multiforme. Expert Opin Pharmacother. 2011 Apr;12(5):825-33. doi: 10.1517/14656566.2011.566558. Epub 2011 Mar 9. Review. PubMed PMID: 21385110.

9: Illum H. Irinotecan and radiosensitization in rectal cancer. Anticancer Drugs. 2011 Apr;22(4):324-9. doi: 10.1097/CAD.0b013e3283425c14. Review. PubMed PMID: 21160419.

10: Heinemann V, Hoff PM. Bevacizumab plus irinotecan-based regimens in the treatment of metastatic colorectal cancer. Oncology. 2010;79(1-2):118-28. doi: 10.1159/000314993. Epub 2010 Nov 22. Review. PubMed PMID: 21088438.

11: Montagnani F, Chiriatti A, Licitra S, Aliberti C, Fiorentini G. Differences in efficacy and safety between capecitabine and infusional 5-fluorouracil when combined with irinotecan for the treatment of metastatic colorectal cancer. Clin Colorectal Cancer. 2010 Oct;9(4):243-7. doi: 10.3816/CCC.2010.n.036. Review. PubMed PMID: 20920997.

12: Nagaiah G, Almubarak M, Khan M, Altaha R. Cerebrospinal fluid leak during treatment with bevacizumab and irinotecan after carmustine-impregnated wafers placement in patients with grade 2 oligodendroglioma and glioblastoma multiforme: report of two cases and review of literature. Cancer Invest. 2010 Dec;28(10):1048-53. doi: 10.3109/07357907.2010.483499. Epub 2010 Sep 27. Review. PubMed PMID: 20873990.

13: Oostendorp LJ, Stalmeier PF, Pasker-de Jong PC, Van der Graaf WT, Ottevanger PB. Systematic review of benefits and risks of second-line irinotecan monotherapy for advanced colorectal cancer. Anticancer Drugs. 2010 Sep;21(8):749-58. doi: 10.1097/CAD.0b013e32833c57cf. Review. PubMed PMID: 20616701.

14: Marsh S, Hoskins JM. Irinotecan pharmacogenomics. Pharmacogenomics. 2010 Jul;11(7):1003-10. doi: 10.2217/pgs.10.95. Review. PubMed PMID: 20602618; PubMed Central PMCID: PMC2927346.

15: Xu T, Chen J, Lu Y, Wolff JE. Effects of bevacizumab plus irinotecan on response and survival in patients with recurrent malignant glioma: a systematic review and survival-gain analysis. BMC Cancer. 2010 Jun 2;10:252. doi: 10.1186/1471-2407-10-252. Review. PubMed PMID: 20525214; PubMed Central PMCID: PMC2891637.

16: Fujita K, Sparreboom A. Pharmacogenetics of irinotecan disposition and toxicity: a review. Curr Clin Pharmacol. 2010 Aug;5(3):209-17. Review. PubMed PMID: 20406168.

17: Farhat FS, Kattan J, Ghosn MG. Role of capecitabine and irinotecan combination therapy in advanced or metastatic gastric cancer. Expert Rev Anticancer Ther. 2010 Apr;10(4):541-8. doi: 10.1586/era.09.179. Review. PubMed PMID: 20397919.

18: Cartwright T, McCollum D, Boehm KA. Dosing considerations for capecitabine-irinotecan regimens in the treatment of metastatic and/or locally advanced colorectal cancer. Am J Clin Oncol. 2010 Jun;33(3):307-13. doi: 10.1097/COC.0b013e3181d27361. Review. PubMed PMID: 20375835.

19: Hu ZY, Yu Q, Zhao YS. Dose-dependent association between UGT1A1*28 polymorphism and irinotecan-induced diarrhoea: a meta-analysis. Eur J Cancer. 2010 Jul;46(10):1856-65. doi: 10.1016/j.ejca.2010.02.049. Epub 2010 Mar 23. Review. PubMed PMID: 20335017.

20: Fujiwara Y, Minami H. An overview of the recent progress in irinotecan pharmacogenetics. Pharmacogenomics. 2010 Mar;11(3):391-406. doi: 10.2217/pgs.10.19. Review. PubMed PMID: 20235794.